Gregory’s son, Christian Gregory, announced his father’s passing on social media, thanking fans for their outpouring of support and asking for privacy while the family grieves. The comedian was admitted to the hospital a week earlier with symptoms related to heart failure. His longtime publicist, Steve Jaffe, said Gregory died surrounded by his family, including his wife of 58 years, Lillian Gregory.

A St. Louis native, Gregory was one of the first Black performers to connect with White audiences, at a time when segregation in the South and more subtle racism in the North blocked the aspirations of Black entertainers. His break came in 1961 when he filled in for a White comedian at Hugh Hefner’s Playboy Club in Chicago.

He didn’t shy away from addressing the evils of racism in his routine. The New York Times said his approach was “to neither scold nor lecture” White audiences but to use “wry observations.” He would famously observe, for example, that a Southern moderate is “a cat that’ll lynch you from a low tree.”

His activism stated in 1962 with a demonstration in Mississippi for Black voting rights. Over the years, he was arrested numerous times and used those experiences to condemn White racism.